socks or no socks? people find it weird from where I am to wear no socks with boats shoes or vans, and such.

It depends. I wear no socks with my vans when i'm wearing shorts or cuffed chinos. Otherwise I do wear socks. All the time. If you don't like the sockless feel you can buy some ankle socks or something.
Oh yeah, never ever wear socks with boat shoes in the summer. You can start wearing wool socks when it's getting colder.